2026 Highland Trail 550

July 21, 2026

Words by Hannah Simon

Photos by Gavin Kaps

I’ve had to pinch myself more than a couple times since getting to ride Highland Trail in May.

The extreme conditions you exist under cause ultra racing to feel like a bit of a dream. Deprivation of all sorts: sleep, calories, comfort. Paired with over stimuli of all kinds: sweeping views, freezing temperatures, resistant terrain. In the scheme of races, Highland Trail feels like the paramount challenge. It’s one of those dreams that has sat on my calendar for the last couple of years. A bit daunting. Fully out of my comfort zone. One of the furthest climates from the desert riding where I feel most at home.

The thing about the Scottish Highlands is that the challenges are predictable. It is a fact that it will rain. It is guaranteed to be cold. The trail will be slower than you want. You’ll be hiking your bike up that climb and likely down a lot of the descent, too. You’ll have to get off your bike to clear that water bar. Your front wheel will sink into that bog. These are the run-of-the-mill warnings that you get before you even ask.

The best part is that the surprises in the Highlands are pleasant. An afternoon sun each day. A chance to air out my damp kit and spread my toes. A hotel offering their dryer. A Chinese place staying open late. A dram of single-malt Scotch with a healthy dose of camaraderie at the base of a climb. The little surprises of the Highlands are not to be expected, but they are always pleasant.

Predictably Difficult

Armed with four pairs of socks and a newly-waterproofed rain kit, I went into the race expecting to be uncomfortable. I knew that the sky would open up anytime it wanted and that I’d be saturated through like the ground of a bog. For the first time in a race, I found myself keeping my rain jacket on for the majority of the time that I was riding.

What I hadn’t realized was my ignorance to riding a bicycle through a bog. This is an experience that seems uniquely UK: on the sunniest afternoon the entire ground is still so saturated such that it does not need to be actively raining in order to absolutely soak your feet. The trail remains mostly obvious, but it cannot always be trusted. Often, you can see the remains of other riders who attempted alternative lines to avoid the puddles. I realized as I trudged through the mud that I needed to learn how to ‘read the bog.’ The length of the puddle does not matter at all. If there are floating blades of grass it’s likely softer than you think. Consult the edges of the path, but almost always commit to riding the trail. It’s the safest bet. You’re bound to sink your front wheel eventually. Laugh at yourself and keep playing the game. You’ll get through it eventually.

Along with the fairly reliable afternoon sun came the guarantee that it would rain every night. This made hunting out a covered bivvy spot a requirement and meant that I had to push a little further than I would have liked on a couple of the nights.

Night four, after leaving Oykel Bridge for the second time, with a dram of Scotch from the whisky trail angels warming my insides, I set out into the night with my eye on Knockdamph bothy. About 5km into my 15km uphill journey, it began to rain. I passed the Schoolhouse bothy, which had no less than 10 bikes leaning up on the outside. The rain was still light and I was feeling good, so I decided to press on into the night. How much further would 10km be?

Very soon after I’d passed up the chance to sleep inside, the rain started coming down in droves. The already-saturated trail swelled and water kicked up as I pedaled, soaking me from all angles. I was struggling to see through the downpour and the last 5km to Knockdamph bothy was the slowest 5km I’ve experienced in a while. Once arrived, there were tents set up all around and a car parked out front. One of the rooms was covered in tarps waiting to be painted and the door to the other was shut. Unaware of bothy etiquette, I hesitated before poking my head into the closed room. There was a fire lit and the warmth hit my rain-chilled face like a gentle embrace. “Hullo!” a Scottish accent came from the corner of the room out of sight. I began apologizing immediately and moved to leave the space. The voice spoke again with heavy reassurance and a welcoming tone. “Sorry for the mess, I’ve been renovating! There’s plenty of room in here and upstairs. Please make yourself at home.” Still shy about my intrusion, I thanked him and wandered upstairs to the unoccupied room. It was not cozy with firelight, but it was out of the pouring rain and I was grateful.

The next day I was validated in my decision to brave the rain. Several of the riders who had opted for the Schoolhouse bothy spoke of how loud and stinky it was inside. I was even more grateful for my solitude then. It’s tricky to find comfortable places to rest along the trail and it’s common that you end up sharing them with other racers, which can sometimes cause disruption in the most precious resource of sleep. It’s all part of the game.

I find that racing a route from a Grand Depart to be mostly an advantage. There’s comfort in knowing that you aren’t the only one out on the route, but it does have its drawbacks. One of those is witnessing everyone scratching around you. This year, we had a front row seat to the scratch show in the form of a WhatsApp chat dedicated to riders reporting that they had officially scratched. Broken wheels, snapped derailleurs, failing knees, sore bums. Even the organizer, who was out for an ITT, scratched after Coffin Road with the claim that he just simply wasn’t “tough enough for the conditions.” You can imagine what each of these notifications does to your psyche while racing. The group chat served as a laundry list of reasons why you may need to scratch, too.

60 kilometers into day two, I got a hankering for an ice cream and an espresso. This is a common occurrence for me while racing. This desire hit as I was passing by an inn with their door open. Missing the bike leaned-up out front, I was surprised to find a rider sitting in the back of the cafe. We struck up conversation and he shared that he’d decided to scratch. Pesky, chronic knee pain that he’d dealt with before caused him to realize he wasn’t enjoying himself at all. “I’ve been to all of these beautiful places in the world to ride my bike and I’ve missed seeing any of them with my head down in pain.” His epiphany hit me in the chest. He wasn’t just processing a scratch from Highland Trail; he was contemplating why he pursues ultra racing at all.

Though I’ve been lucky to not endure physical pain like he described, I have had my fair share of “why?” while in the midst of a race effort. Mine usually comes from a desire to stop and see the sights. I grapple with balancing between pushing myself and also still experiencing the world around me. I was grateful to have listened to my craving for espresso and ice cream. Sharing that moment in the cafe helped keep me grounded in my determination to have a good time above all else.

Surprisingly Pleasant

I realize that the UK is a big island, indicating that it has a lot of coastline, but when I think of Scotland I don’t think about the ‘Scottish coast.’ I don’t imagine big, sheer cliffs, crashing blue and teal waves, sandy beaches and sunshine. I got lucky arriving in Drumbeg with the sun high in the sky and not a cloud in sight. I’d pulled my sleep kit out, dampened from the rain the night before, and laid it across the concrete to dry while I ate my Drumbeg Stores chicken caesar sandwich. Through the afternoon, I rode the rolling hills of the paved coastal road and admired the quaint farm homes and roadside shops catering to tourists. I was having such a blast that I’d completely forgotten that Ruby Beardsall was chasing me down. Known for her proficiency on her Cannondale SuperSix (yes, that’s a cyclocross bike!!), Ruby had finished Dale’s Divide, her first ultra, a few weeks earlier in second place. We had yo-yo’d with one another throughout the route, usually ending up in a similar place each night.

She passed me for the last time on the way into a short singletrack section off the coastal road. As she blasted by, it occurred to me that she wasn’t having the same marveling-at-the-sheep moment that I was. The UK is her home. The Scottish coast is only a weekend trip away. I knew then and there that I wouldn’t catch her again. I remembered the rider at the hostel who had scratched. I reminded myself that I had come to the race to see the beauty of the highlands. For me, this experience may be once in my lifetime. I didn’t want to spend my time racing through Scotland with my head down. (Also, just to be clear, even if I abandoned all self-preservation and enjoyment, Ruby absolutely would have still beaten me. She’s a machine.)

When I released the expectation of ‘keeping up,’ I felt myself relax into the rhythm of riding my bike for me. Still pushing myself. Still dealing with discomfort, but keeping my head up along the way.

On my last day on the trail I approached Devil’s Staircase, the final significant hike-a-bike on the route, right around noon. With over 800 kilometers of trail behind me, including Coffin Road, Fisherfield, Ben Alder and Glen Affric, I wasn’t necessarily concerned about Devil’s Staircase. The sky was its usual mix of big ol’ storm and random blue sky. I had plenty of daylight to work with and I stopped for a proper grocery store lunch in Kinlochleven right before starting the climb. Classically, the Staircase is hiked from south to north, the opposite direction in which I was traveling. For a bike, it makes perfect sense to do it ‘backwards.’ Ride up (some of) the less-steep northern side and descend (most of) the rocky, steep southern face.

I’m proud to report that I rode all the way to the top of the paved portion of the road (if you know, you know.. small flex). As the singletrack started, I relinquished myself to hiking and the comments began: “You’re taking your bike all the way up there?” “Wow, you’re so brave!” “How will you get down the other side?” It seemed that every West Highland Way passerby (at noon there were numerous of them) had something to say about my endeavor. I started to worry. What was I about to encounter? Was the last 60 kilometers of the Highland Trail going to be the part that finally broke me?

My common mantra amidst the difficulty of an ultra is that “the only way out is through.” Maybe Devil’s Staircase would be the worst of them. There was a simple way to find out.

At 2pm, I crested the top of the climb and looked around for the rest of it.. “That’s it?” I said out loud. Don’t get me wrong, the view was magnificent, but I had arrived with very little resistance. It only hailed on me once. I didn’t hoist my bike on my back at all. The pleasant surprises just kept flowing. The descent was chunky and riddled with hikers, but it was fun to pick my way through the lines. I adopted an approach from my time learning the bogs: the trail is a suggestion, everything is a line. Finding the path of least resistance, I got to the base of the staircase with a smile on my face.

The final surprise of the race, which left me in tears, was the crowd of people ready to hug me at the finish. I had been blasting Harry Styles’ new album in my left headphone and was enjoying a poetic finish to “Paint By Numbers” when the crowd came into view on the last descent: Matt and Markus, who had finished just before me. Sebastian, who I’d ridden with on-and-off until he had to scratch. Bryn, who I hadn’t met because he blasted off from the beginning and came 6th. Suzie, who had just arrived from her own off-route adventure back to the start. Lee and Alice, who had come back from their home on the western coast just to see the finishers, stayed just long enough to cheer me in before heading back home. I wish I had a photo of the moment, (especially if you were there and I’ve forgotten, I’m so sorry!) but I realized that I remember every finish of every ultra I’ve done. Maybe not every single name and face that were present, but every scene of rolling into the end of a route. Every feeling of accomplishment, happiness, and relief has stuck with me every time.

These are just a few snippets of the incredible stories I collected during my five days on the route. I can recall countless other moments of kindness from folks along the route, drams of whisky with Donnie and Richie, sharing rainbows with strangers and resisting the urge to scoop up every little, snow-white lamb I passed. There’s something really special about Highland Trail. The things it puts you through, the limits it pushes, the camaraderie it inspires. I feel really fortunate to join the ranks of those who have experienced it. I hope these reflections do some part in encouraging you to consider the challenge, too.

Follow Hannah’s adventures on Instagram @hannahmsimon_